Eco-Efficient One-Pot Synthesis of Quinazoline-2,4(1H,3H)-diones at Room Temperature in Water

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  • Tian Xin-Chuan
    Department of Chinese Traditional Herbal, Agronomy College, Sichuan Agricultural University
  • Huang Xing
    Department of Chinese Traditional Herbal, Agronomy College, Sichuan Agricultural University
  • Wang Dan
    Department of Chinese Traditional Herbal, Agronomy College, Sichuan Agricultural University
  • Gao Feng
    Department of Chinese Traditional Herbal, Agronomy College, Sichuan Agricultural University

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  • Eco-Efficient One-Pot Synthesis of Quinazoline-2,4(1<i>H</i>,3<i>H</i>)-diones at Room Temperature in Water

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An efficient one-pot synthesis of quinazoline-2,4(1H,3H)-diones was developed. First, the reactions of anthranilic acid derivatives with potassium cyanate afforded the corresponding urea derivatives. Then, cyclization of the urea derivatives with NaOH afforded the monosodium salts of benzoylene urea. Finally, HCl treatment afforded the desired products in near-quantitative yields. This is an eco-efficient method because all the reactions were carried out in water, and the desired products were obtained simply by filtration. The aqueous filtrate was the only waste generated from the reaction. We scaled up the reaction to 1 kg starting material, thus establishing an alternative approach for the green synthesis of quinazoline-2,4(1H,3H)-diones in the chemical and pharmaceutical industries.

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